EP2406239B1 - Composés carbamates cycliques utiles dans des compositions durcissables sous l'action d'une énergie - Google Patents

Composés carbamates cycliques utiles dans des compositions durcissables sous l'action d'une énergie Download PDF

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Publication number
EP2406239B1
EP2406239B1 EP10708581.3A EP10708581A EP2406239B1 EP 2406239 B1 EP2406239 B1 EP 2406239B1 EP 10708581 A EP10708581 A EP 10708581A EP 2406239 B1 EP2406239 B1 EP 2406239B1
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Prior art keywords
cyclic carbamate
acrylate
group
compound
curable
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EP10708581.3A
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German (de)
English (en)
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EP2406239A1 (fr
Inventor
Shaun Herlihy
Brian Rowatt
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Sun Chemical BV
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Sun Chemical BV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31935—Ester, halide or nitrile of addition polymer

Claims (15)

  1. Composé carbamate cyclique, qui contient un système de noyau carbamate cyclique de 5 à 7 chaînons lié par l'intermédiaire d'un groupe alkylène ou polyéther à un groupe 3-amino propionate ou à un groupe 3-amino-2-méthyl propionate, dans lequel l'atome d'azote du carbamate cyclique est lié au groupe alkylène ou polyéther, ledit composé carbamate cyclique étant le produit d'une réaction d'addition de Michael d'une amine aliphatique et d'un carbamate cyclique comportant un groupe fonctionnel (méth)acrylate et un système de noyau carbamate cyclique de 5 à 7 chaînons.
  2. Composé carbamate cyclique selon la revendication 1, comprenant en outre un groupe fonctionnel qui est durcissable dans une réaction de durcissement par voie radicalaire, qui comprend un groupe éthyléniquement insaturé.
  3. Composé carbamate cyclique selon la revendication 1, qui est le produit d'une réaction d'addition de Michael de : une amine aliphatique ; un carbamate cyclique comportant un groupe fonctionnel (méth)acrylate et un système de noyau carbamate cyclique de 5 à 7 chaînons ; et un groupe acrylate multifonctionnel.
  4. Composé carbamate cyclique selon l'une quelconque des revendications précédentes, dans lequel le carbamate cyclique de type acrylate est une N-(2-acryloyloxyalkyl)oxazolidinone.
  5. Composé carbamate cyclique selon l'une quelconque des revendications précédentes, dans lequel l'amine aliphatique est une diamine.
  6. Composé carbamate cyclique selon l'une quelconque des revendications précédentes dans lequel le système de noyau carbamate cyclique est un noyau oxazolidinone à 5 chaînons.
  7. Composé carbamate cyclique selon l'une quelconque des revendications précédentes, comprenant un composé répondant à la formule (I) :
    Figure imgb0025
     dans laquelle :
    R1 représente un groupement répondant à la formule (II) :
    Figure imgb0026
     dans laquelle m vaut 1, 2 ou 3 ; n vaut de 1 à 8 ; o vaut de 1 à 10 ; et chaque R est indépendamment choisi parmi l'atome d'H et un groupe méthyle ;
    R2 représente une chaîne aliphatique, facultativement liée à un groupement répondant à la formule (III) :
    Figure imgb0027
    chaque R3 est choisi parmi :
    - un groupe aliphatique, facultativement lié à un autre groupement répondant à la formule (III),
    - un autre groupement répondant à la formule (II), ou
    - une unité contenant un groupe acrylate ou un autre groupe fonctionnel qui est durcissable dans une réaction de durcissement par voie radicalaire ;
    ou R3 et R4 forment ensemble une chaîne aliphatique ; et
    R4 et R5 sont chacun indépendamment choisis parmi :
    - un groupe aliphatique,
    - un autre groupement répondant à la formule (II), ou
    - une unité contenant un groupe acrylate ou un autre groupe fonctionnel qui est durcissable dans une réaction de durcissement par voie radicalaire,
    ou
    comprenant un composé répondant à la formule (IV) :
    Figure imgb0028
     dans laquelle :
    m vaut 1, 2 ou 3 ;
    n vaut de 1 à 8 ;
    o vaut de 1 à 10 ;
    chaque R est indépendamment choisi parmi l'atome d'H et un groupe Mé ;
    X représente un groupe lieur aliphatique ; et
    chacun des groupes R1a, R1b et R1c est indépendamment choisi parmi un groupe aliphatique, un groupement répondant à la formule (II) tel que défini ci-dessus, ou une unité contenant un groupe acrylate ou un autre groupe fonctionnel qui est durcissable dans une réaction de durcissement par voie radicalaire ; ou
    R1a et R1b forment ensemble un autre groupe lieur aliphatique.
  8. Composé carbamate cyclique selon la revendication 7, dans lequel le composé comprend au moins deux groupements répondant à la formule (II).
  9. Composé carbamate cyclique selon l'une quelconque des revendications précédentes, comprenant au moins un groupe fonctionnel acrylate.
  10. Composition durcissable sous l'action d'une énergie comprenant le composé carbamate cyclique selon l'une quelconque des revendications précédentes.
  11. Composition durcissable sous l'action d'une énergie selon la revendication 10, laquelle composition est durcissable par exposition à des rayonnements UV et laquelle composition comprend un photoinitiateur de type clivage.
  12. Procédé de préparation d'un composé carbamate cyclique, comprenant l'étape consistant à faire réagir (i) un carbamate cyclique de type acrylate avec (ii) une amine aliphatique, et facultativement (iii) un groupe acrylate multifonctionnel, dans lequel le carbamate cyclique de type acrylate contient un système de noyau carbamate cyclique de 5 à 7 chaînons lié par l'intermédiaire d'un alkylène ou d'un polyéther à un groupe fonctionnel (méth)acrylate, et dans lequel l'atome d'azote du carbamate cyclique est lié au groupe alkylène ou polyéther.
  13. Utilisation d'un composé carbamate cyclique tel que défini dans l'une quelconque des revendications 1 à 9 comme fixateur d'oxygène dans une composition durcissable sous l'action d'une énergie.
  14. Procédé de revêtement ou d'impression d'un substrat comprenant les étapes suivantes : (a) application de la composition durcissable sous l'action d'une énergie selon la revendication 10 ou la revendication 11 sur le substrat, et (b) durcissement de la composition.
  15. Article revêtu ou imprimé comprenant une combinaison d'un substrat et d'une image revêtue ou imprimée durcie comprenant le composé carbamate cyclique selon l'une quelconque des revendications 1 à 9.
EP10708581.3A 2009-03-13 2010-03-11 Composés carbamates cycliques utiles dans des compositions durcissables sous l'action d'une énergie Active EP2406239B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15993009P 2009-03-13 2009-03-13
PCT/GB2010/000441 WO2010103281A1 (fr) 2009-03-13 2010-03-11 Composés carbamates cycliques utiles dans des compositions durcissables sous l'action d'une énergie

Publications (2)

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EP2406239A1 EP2406239A1 (fr) 2012-01-18
EP2406239B1 true EP2406239B1 (fr) 2016-09-14

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Country Link
US (1) US9428471B2 (fr)
EP (1) EP2406239B1 (fr)
JP (1) JP5731413B2 (fr)
KR (1) KR20110136850A (fr)
CN (1) CN102348696B (fr)
CA (1) CA2754712A1 (fr)
ES (1) ES2605472T3 (fr)
WO (1) WO2010103281A1 (fr)
ZA (1) ZA201106470B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3033399T3 (pl) * 2013-08-12 2018-03-30 Basf Se Farba drukarska do druku strumieniowego zawierająca n-winyloksazolidynon
WO2016092548A1 (fr) * 2014-12-09 2016-06-16 Cronus Cyber Technologies Ltd Détection d'empreinte digitale de système d'exploitation
KR102402399B1 (ko) * 2016-08-10 2022-05-25 아르끄마 프랑스 시클릭 구조 요소, 우레탄 / 우레이도 연결 및 자유 라디칼-중합성 작용기를 함유하는 화합물
US20230287230A1 (en) 2020-07-31 2023-09-14 Sun Chemical Corporation Self-initiated energy curable ink compositions
WO2022055625A1 (fr) 2020-09-10 2022-03-17 Sun Chemical Corporation Compositions d'encre durcissables par une énergie del

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US2905690A (en) 1959-09-22 Vinylation of oxazolidinones
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US3268485A (en) 1963-05-01 1966-08-23 Dow Chemical Co Polymers of 3-(2-hydroxyalkyl) oxazolidinone acrylates and methacrylates
US4675374A (en) * 1984-03-26 1987-06-23 Gus Nichols Solventless polymeric composition reaction product of (1) adduct of amine and acrylate with (2) polyacrylate
US4639472A (en) 1984-12-17 1987-01-27 The Dow Chemical Company N-vinyl-2-oxazolidinones as reactive diluents in actinic radiation curable coatings
US4933462A (en) 1988-07-25 1990-06-12 The Dow Chemical Company Synthesis of 3-(2-hydroxyethyl)-2-oxazolidinones
GB9014299D0 (en) 1990-06-27 1990-08-15 Domino Printing Sciences Plc Ink composition
US5358946A (en) * 1992-05-29 1994-10-25 The Du Pont Merck Pharmaceutical Company Heterocycle-substituted amides, carbamates and ureas as agents for the treatment of atherosclerosis
JP3698724B2 (ja) * 1993-11-22 2005-09-21 ファルマシア・アンド・アップジョン・カンパニー 置換−ヒドロキシアセチルピペラジンフェニルオキサゾリジノンのエステル
US6965019B2 (en) 2000-04-03 2005-11-15 Sun Chemical Corporation Mono-and bis-hydrazone pigments
TW200500360A (en) * 2003-03-01 2005-01-01 Astrazeneca Ab Hydroxymethyl compounds
KR100854211B1 (ko) * 2003-12-18 2008-08-26 동아제약주식회사 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물
TWI389897B (zh) * 2005-02-22 2013-03-21 Chugai Pharmaceutical Co Ltd 1- (2H) -isoquinolinone derivatives
TWI357902B (en) * 2005-04-01 2012-02-11 Lg Life Science Ltd Dipeptidyl peptidase-iv inhibiting compounds, meth
CA2570090C (fr) 2006-12-06 2014-08-19 Brightside Technologies Inc. Representation et reconstitution d'images a plage dynamique etendue

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Publication number Publication date
EP2406239A1 (fr) 2012-01-18
US9428471B2 (en) 2016-08-30
CA2754712A1 (fr) 2010-09-16
US20120015159A1 (en) 2012-01-19
KR20110136850A (ko) 2011-12-21
ZA201106470B (en) 2012-05-30
JP2012520277A (ja) 2012-09-06
ES2605472T3 (es) 2017-03-14
WO2010103281A1 (fr) 2010-09-16
CN102348696A (zh) 2012-02-08
CN102348696B (zh) 2015-06-17
JP5731413B2 (ja) 2015-06-10

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